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Strange cocktails that "work"

I think that there are lots of drinks that fit the bill here. Some things just don't sound like they'll go well together--but they do. When I first came across a Sazerac, I couldn't imagine that it would taste good. Absinthe is absinthe--it didn't strike me as something that would willingly share a glass with anything else (although I think that the first absinthe I had was in a champagne cocktail, and it was very nice). But it's a perfect cocktail. Likewise, I could imagine any number of whiskeys in a cocktail, but not Scotch. It just didn't seem right. Then somebody bought me a Rob Roy and I saw that the world held many possibilities that I had to accept (although it isn't my drink of choice). All that having been said, I'm still a proponent for "simple is better." There are so many amazing, venerable cocktails that I don't find myself craving a eggnog frappe with grapefruit bitters, vintage Anejo tequila and craft-distilled root beer liqueur.
 
Not sure it's 'strange' I tend to think of it as an Italianish version of a Manhattan. the quiet italian gentleman: jim beam rye, carpano antique, disaronna amaretto, campari
 

Hirsute

Used to have fun with Commander Yellow Pantyhose
Here are a couple of oddballs that work (I promise they're way better than they sound):

Brave Bull - equal parts tequila and kahlua
Snowshoe - equal parts bourbon and peppermint schnapps
 

martym

Unacceptably Lasering Chicken Giblets?
Tequila (Corzo is my favorite) with cranberry juice or cran-grape juice.
Really goes down well.
 
Tequila (Corzo is my favorite) with cranberry juice or cran-grape juice.
Really goes down well.

Oh yeah! This used to be one of my favorite drinks, but now I cannot drink cranberry juice due to possible adverse drug interactions. I liked mine with a lemon wedge squeezed in.
 
First cocktail I ever had was an Alabama Slammer. I can't now imagine Southern Comfort or Amaretto being of any benefit in a mixed drink, but combining them both with vodka and sloe gin (and I think it was cranberry juice) was something truly memorable.

I might try and experiment with Lemon Hart rum instead of the vodka and cherry juice concentrate instead of the cranberry.

Who'm I kidding - I'm just going to drink the Lemon Hart straight from the bottle while I look at the other ingredients....
 
It sounds distinctly low-rent and like a poor-man's margarita, but the Paloma mixed-drink is awesome.

Ingredients:

2 oz Blanco tequila
4-6 oz Grapefruit soda (Jarritos from Mexico is the best, but Squirt or Fanta will work in a pinch)
Juice of half a lime.
Tiny pinch salt.
 

Hirsute

Used to have fun with Commander Yellow Pantyhose
It sounds distinctly low-rent and like a poor-man's margarita, but the Paloma mixed-drink is awesome.

Ingredients:

2 oz Blanco tequila
4-6 oz Grapefruit soda (Jarritos from Mexico is the best, but Squirt or Fanta will work in a pinch)
Juice of half a lime.
Tiny pinch salt.

I've had a Paloma with a little muddled basil and it was awesome!
 
It sounds distinctly low-rent and like a poor-man's margarita, but the Paloma mixed-drink is awesome.

Ingredients:

2 oz Blanco tequila
4-6 oz Grapefruit soda (Jarritos from Mexico is the best, but Squirt or Fanta will work in a pinch)
Juice of half a lime.
Tiny pinch salt.

Actually, the Paloma is the most popular tequila cocktail in Mexico (among Mexicans).
 
... Another good one is a tequila screwdriver - cheap tequila, orange juice to taste, repeat multiple times, and make no plans for the rest of the evening. Or the next morning, either.
Add a bit of Grenadine, and you have a Tequila Sunrise.
 
Black label and tonic ... So good... Didn't think it was weird but every time I order it the bartender needs to verify that that's what I want... I drank it in Chicago... Maybe it's weird now that I live in texas
 
Black label and tonic ... So good... Didn't think it was weird but every time I order it the bartender needs to verify that that's what I want... I drank it in Chicago... Maybe it's weird now that I live in texas

I tried google to no avail. What is "Black label"?
 
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